An optically active sulfoxide compound is an important intermediate as an asymmetric aid in asymmetric synthesis.
The optically active sulfoxide compound is used as an asymmetric aid in synthesis of an optically active allyl alcohol derivative (see Patent Document 1, for example). The optically active sulfoxide compound is used as an asymmetric aid also in synthesis of various optically active compounds (see Non-patent Documents 1 and 2, for example).
A large number of pharmaceutical agents containing optically active sulfoxide compound sites have been developed, which indicates that a technique of asymmetric oxidation of sulfide compounds into optically active sulfoxide compounds is useful as a process for producing pharmaceutical agents.
As a method for producing an optically active sulfoxide compound from a sulfide compound, a reaction using titanium-tartaric acid ester as a catalyst (see Non-patent Documents 3 and 4, for example), a reaction using titanium-optically active binaphthol as a catalyst (see Non-patent Documents 5 and 6, for example), a reaction using a metalloporphyrin complex as a catalyst (see Non-patent Documents 7 and 8, for example), a reaction using a metallosalen complex as a catalyst (see Non-patent Documents 9, 10, and 11, for example), and the like are known.
In recent years, a method in which a hydrogen peroxide solution is used as an oxidizing agent has been investigated actively. For example, a reaction using a vanadium complex as a catalyst (see Non-patent Documents 12, 13, 14, 15, and 16, for example), a reaction using an iron complex as a catalyst (see Non-patent Documents 17, 18, and 19, for example), and a reaction using a tungsten complex as a catalyst (see Non-patent Document 20, for example), all of which uses hydrogen peroxide as an oxidizing agent, are known.
[Patent Document 1]
Japanese Patent Application Publication No. JP-A-7-82195
[Non-patent Document 1]
Chem. Ind. 15, 636 (1994)
[Non-patent Document 2]
Acc. Chem. Res. 20, 72 (1987)
[Non-patent Document 3]
J. Am. Chem. Soc. 106, 8188 (1984)
[Non-patent Document 4]
J. Org. Chem. 60, 8086 (1995)
[Non-patent Document 5]
Tetrahedron Lett. 33, 5391 (1992)
[Non-patent Document 6]
J. Org. Chem. 58, 4529 (1993)
[Non-patent Document 7]
Tetrahedron Lett. 23, 1685 (1982)
[Non-patent Document 8]
J. Org. Chem. 55, 3628 (1990)
[Non-patent Document 9]
Chem. Lett. 1483 (1986)
[Non-patent Document 10]
Tetrahedron Lett. 33, 7111 (1992)
[Non-patent Document 11]
Tetrahedron Lett. 35, 1887 (1994)
[Non-patent Document 12]
Synlett, 1055-1060 (2002)
[Non-patent Document 13]
Synlett, 161-163 (2002)
[Non-patent Document 14]
Org. Lett. 5, 1317-1320 (2003)
[Non-patent Document 15]
J. Org. Chem. 69, 8500-8503 (2004)
[Non-patent Document 16]
Angew. Chem. Int, Ed., 44, 7221-7223 (2005)
[Non-patent Document 17]
Angew. Chem. Int, Ed., 42, 5487-5489 (2003)
[Non-patent Document 18]
Angew. Chem. Int, Ed., 43, 4225-4228 (2004)
[Non-patent Document 19]
Chem. Eur. J., 11, 1086-1092 (2005)
[Non-patent Document 20]
Tetrahedron Asymmetry, 14, 407-410 (2003)